The Recent Developments in Biobased Polymers toward General and Engineering Applications: Polymers that are Upgraded from Biodegradable Polymers, Analogous to Petroleum-Derived Polymers, and Newly Developed

Steinbuechel, A. (2001). Biopolymers, Wiley-VCH.

Domb, A.J., Kost, J., and Wiseman, D.M. (1997). Handbook of Biodegradable Polymers, Harwood Academic Publishers.

Klass, D.L. (1998). Biomass for Renewable Energy, Fuels, and Chemicals, Academic Press.

Mohsenzadeh, 2017, Bioethylene Production from Ethanol: A review and Techno-economical Evaluation, ChemBioEng Rev., 4, 75, 10.1002/cben.201600025

Atabani, 2012, A comprehensive review on biodiesel as an alternative energy resource and its characteristics, Renew. Sust. Energy Rev., 16, 2070, 10.1016/j.rser.2012.01.003

Corma, 2007, Chemical Routes for the Transformation of Biomass into Chemicals, Chem. Rev., 107, 2411, 10.1021/cr050989d

Im, S.S., Kim, Y.H., Yoon, J.S., and Chin, I.-J. (2005). Biobased-Polymers: Recent Progress, Wiley-VCH.

Kimura, 2009, Molecular, Structural, and Material Design of Bio-Based Polymers, Polym. J., 41, 797, 10.1295/polymj.PJ2009154

Kimura, Y. (2013). Chapter 1, General introduction: Overview of the current development of biobased polymers. Bio-Based Polymers, CMC Publishing Co., Ltd.. [1st ed.].

Babu, 2013, Current progress on bio-based polymers and their future trends, Prog. Biomater., 2, 1, 10.1186/2194-0517-2-8

Steinbuchel, A., and Doi, Y. (2002). Polylactide. Biopolymers, Vol.4, Polyesters III, Wiley-VCH Verlag GmBH.

Tsuji, 2005, Poly(lactide) Stereocomplexes: Formation, Structure, Properties, Degradation, and Applications, Macromol. Biosci., 5, 569, 10.1002/mabi.200500062

Fukushima, 2006, Stereocomplexed polylactides (Neo-PLA) as high-performance bio-based polymers: Their formation, properties, and application, Polym. Int., 55, 626, 10.1002/pi.2010

(2017, August 16). National Renewable Energy Laboratory Report, Available online: https://www.nrel.gov/docs/fy04osti/35523.pdf.

(2017, July 15). PRO-BIP2009. Available online: https://www.uu.nl/sites/default/files/copernicus_probip2009_final_june_2009_revised_in_november_09.pdf.

(2017, August 16). Bio-Based Chemicals. Available online: http://www.iea-bioenergy.task42-biorefineries.com/upload_mm/b/a/8/6d099772-d69d-46a3-bbf7-62378e37e1df_Biobased_Chemicals_Report_Total_IEABioenergyTask42.pdf.

(2017, August 16). Corbion/Total Announcement. Available online: https://www.total-corbion.com/products/pla-polymers/.

Kimura, Y. (2013). Application of Bio-based Polymers. Bio-Based Polymers, CMC Publishing Co., Ltd.. [1st ed.]. Chapter 5.

Mochizuki, M. (2002). Biopolymers, Vol.4, Polyesters III, Wiley-VCH Verlag GmBH.

Avantium Report (2017, August 16). Renewable Chemicals into Bio-Based Materials: From Lignocellulose to PEF. Available online: http://biobasedperformancematerials.nl/upload_mm/3/5/7/651bed82-390b-4435-a006-7909570de736_BPM%202017%20-%20Speaker%2006%20-%20Ed%20de%20Jong%20-%20Renewable%20chemicals%20into%20bio-based%20materials%20-%20from%20lignocellulose%20to%20PEF.pdf.

Avantium Report (2017, August 16). PEF, a 100% Bio-Based Polyester: Synthesis, Properties & Sustainability. Available online: http://euronanoforum2015.eu/wp-content/uploads/2015/06/PlenaryII_PEF_a_100_bio-based_polyester_Gert-JanGruter_11062015_final.pdf.

Kimura, Y. (2013). Poly(trimethylene terephthalate, PTT). Bio-Based Polymers, CMC Publishing Co., Ltd.. [1st ed.]. Chapter 3.4.

Mochizuki, 2010, Crystallization Behaviors of highly LLA-rich PLA Effects of D-isomer ratio of PLA on the rate of crystallization, crystallinity, and melting point, Sen’I Gakkaishi, 66, 70, 10.2115/fiber.66.P_70

Marega, 1992, Structure and crystallization kinetics of poly(l-lactic acid), Macromol. Chem. Phys., 193, 1599, 10.1002/macp.1992.021930704

Sasaki, 2003, Helix Distortion and Crystal Structure of the α-Form of Poly(l-lactide), Macromolecules, 36, 8385, 10.1021/ma0348674

Lotz, 2001, Crystal Structure of the α-Form of Poly(l-lactide), Macromolecules, 34, 4795, 10.1021/ma001630o

Wasanasuk, 2011, Crystal structure and disorder in poly(l-lactic acid) δ form (α′ form) and the phase transition mechanism to the ordered α form, Polymer, 52, 6097, 10.1016/j.polymer.2011.10.046

Zhang, 2008, Disorder-to-Order Phase Transition and Multiple Melting Behavior of Poly(l-lactide) Investigated by Simultaneous Measurements of WAXD and DSC, Macromolecules, 41, 1352, 10.1021/ma0706071

Zhang, 2005, Crystal Modifications and Thermal Behavior of Poly(l-lactic acid) Revealed by Infrared Spectroscopy, Macromolecules, 38, 8012, 10.1021/ma051232r

Ikada, 1987, Stereocomplex formation between enantiomeric poly(lactides), Macromolecules, 20, 904, 10.1021/ma00170a034

Duan, 2006, Molecular Weight Dependence of the Poly(l-lactide)/Poly(d-lactide) Stereocomplex at the Air−Water Interface, Biomacromolecules, 7, 2728, 10.1021/bm060043t

Serizawa, 2001, Stepwise Assembly of Enantiomeric Poly(lactide)s on Surfaces, Macromolecules, 34, 1996, 10.1021/ma001705o

Hoogsteen, 1990, Crystal structure, conformation and morphology of solution-spun poly(l-lactide) fibers, Macromolecules, 23, 634, 10.1021/ma00204a041

Okihara, 1991, Crystal structure of stereocomplex of poly(l-lactide) and poly(d-lactide), J. Macromol. Sci. Phys., 30, 119, 10.1080/00222349108245788

(2017, August 16). NatureWorks Website. Available online: http://www.natureworksllc.com/What-is-Ingeo.

Niaounakis, M. (2015). Chapter 1, Definition of Terms and Types of Biopolymers. Biopolymers: Applications and Trends, Elsevier. [1st ed.].

Madison, 1999, Metabolic Engineering of Poly(3-Hydroxyalkanoates): From DNA to Plastic, Microbiol. Mol. Biol. Rev., 63, 21, 10.1128/MMBR.63.1.21-53.1999

Valentino, 2014, Polyhydroxyalkanoate (PHA) production from sludge and municipal wastewater treatment, Water Sci. Technol., 69, 177, 10.2166/wst.2013.643

Chatterjee, 2006, Directed evolution of metabolic pathways, Trends Biotechnol., 24, 28, 10.1016/j.tibtech.2005.11.002

Witholt, 1999, Perspectives of medium chain length poly(hydroxyalkanoates), a versatile set of bacterial bioplastics, Curr. Opin. Biotechnol., 10, 279, 10.1016/S0958-1669(99)80049-4

Gerngross, 1995, Enzyme-catalyzed synthesis of poly[(R)-(-)-3-hydroxybutyrate]: Formation of macroscopic granules in vitro, Proc. Natl. Acad. Sci. USA, 92, 6279, 10.1073/pnas.92.14.6279

Ren, 2005, Bacterial Poly(hydroxyalkanoates) as a Source of Chiral Hydroxyalkanoic Acids, Biomacromolecules, 6, 2290, 10.1021/bm050187s

Haywood, 1991, Accumulation of a poly(hydroxyalkanoate) copolymer containing primarily 3-hydroxyvalerate from simple carbohydrate substrates by Rhodococcus sp. NCIMB 40126, Int. J. Biol. Macromol., 13, 83, 10.1016/0141-8130(91)90053-W

Matsumoto, 2009, Production of short-chain-length/medium-chain-length polyhydroxyalkanoate (PHA) copolymer in the plastid of Arabidopsis thaliana using an engineered 3-ketoacyl-acyl carrier protein synthase III, Biomacromolecules, 10, 686, 10.1021/bm8013878

Pollet, E., Averous, L., and Plackett, D. (2011). Biopolymers: New Materials for Sustainable Films and Coatings, Wiley-VCH.

Yokouchi, 1973, Structural studies of polyesters: 5. Molecular and crystal structures of optically active and racemic poly (β-hydroxybutyrate), Polymer, 14, 267, 10.1016/0032-3861(73)90087-6

Hoenich, 2006, Cellulose for medical applications: Past, present, and future, BioResources, 1, 270, 10.15376/biores.1.2.270-280

Dufresne, 2013, Nanocellulose: A new ageless bionanomaterial, Mater. Today, 16, 220, 10.1016/j.mattod.2013.06.004

Vshivkov, 2014, Phase diagrams and rheological properties of cellulose ether solutions in magnetic field, Eur. Polym. J., 59, 326, 10.1016/j.eurpolymj.2014.07.042

Alvarez, 2008, Extraction of cellulose and preparation of nanocellulose from sisal fibers, Cellulose, 15, 149, 10.1007/s10570-007-9145-9

Khan, 2017, Thermoplastic Starch: A Possible Biodegradable Food Packaging Material—A Review, J. Food Proc. Eng., 40, e12447, 10.1111/jfpe.12447

Halley, 2007, A Review of Biodegradable Thermoplastic Starch Polymers, ACS Symp. Ser., 978, 287, 10.1021/bk-2007-0978.ch024

Woortman, 2015, Rheological properties of wheat starch influenced by amylose–lysophosphatidylcholine complexation at different gelation phases, Carbohydr. Polym., 122, 197, 10.1016/j.carbpol.2014.12.063

Woortman, 2014, The effect of temperature and time on the formation of amylose–lysophosphatidylcholine inclusion complexes, Starch, 66, 251, 10.1002/star.201300103

Woortman, 2013, Assessment of the influence of amylose-LPC complexation on the extent of wheat starch digestibility by size-exclusion chromatography, Food Chem., 14, 4318

Thakker, 2012, Succinate production in Escherichia coli, Biotechnol. J., 7, 213, 10.1002/biot.201100061

Zeikus, 1999, Biotechnology of succinic acid production and markets for derived industrial products, Appl. Microbiol. Biotechnol., 51, 545, 10.1007/s002530051431

Xu, 2010, Poly(butylene succinate) and its copolymers: Research, development and industrialization, Biotechnol. J., 5, 1149, 10.1002/biot.201000136

Niaounakis, M. (2015). Biopolymers: Applications and Trends, William Andrew. [1st ed.].

Siracusa, 2015, Poly(butylene succinate) and poly(butylene succinate-co-adipate) for food packaging applications: Gas barrier properties after stressed treatments, Polym. Degrad. Stab., 119, 35, 10.1016/j.polymdegradstab.2015.04.026

Luo, 2010, Synthesis of poly(butylene succinate-co-butylene terephthalate) (PBST) copolyesters with high molecular weights via direct esterification and polycondensation, J. Appl. Polym. Sci., 115, 2203, 10.1002/app.31346

Wu, 2012, High Molecular Weight Poly(butylene succinate-co-butylene furandicarboxylate) Copolyesters: From Catalyzed Polycondensation Reaction to Thermomechanical Properties, Biomacromolecules, 13, 2973, 10.1021/bm301044f

Morschbacker, 2009, Bio-Ethanol Based Ethylene, Polym. Rev., 49, 79, 10.1080/15583720902834791

Braskem report (2017, August 22). Development of Bio-Based Olefins. Available online: http://www.inda.org/BIO/vision2014_659_PPT.pdf.

Hess, 2014, Deconstructing Inherently Safer Technology, Chem. Eng. News, 92, 11

(2017, August 19). The Coca Cola Company Website. Available online: http://www.coca-colacompany.com/plantbottle-technology.

(2017, August 19). Gevo Report. Available online: http://www.gevo.com/wp-content/uploads/PDF/gevo-roadshow-2011-web.pdf.

Carraher, 2017, Cis,cis-Muconic acid isomerization and catalytic conversion to biobased cyclic-C6-1,4-diacid monomers, Green Chem., 19, 3042, 10.1039/C7GC00658F

Colonna, 2011, Synthesis and radiocarbon evidence of terephthalate polyesters completely prepared from renewable resources, Green Chem., 13, 2543, 10.1039/c1gc15400a

Shiramizu, 2011, On the Diels-alder Approach to Solely Biomass-derived Polyethylene terephthalate (PET): Conversion of 2,5-Dimethylfuran and Acrolein into p-Xylene, Chem. Eur. J., 17, 12452, 10.1002/chem.201101580

Gandarias, 2014, Heterogeneous acid-catalysts for the production of furan-derived compounds (furfural and hydroxymethylfurfural) from renewable carbohydrates, Rev. Catal. Today, 234, 42, 10.1016/j.cattod.2013.11.027

Tachibana, 2015, Synthesis and Verification of Biobased Terephthalic Acid from Furfural, Sci. Rep., 5, 8249, 10.1038/srep08249

Collias, 2014, Biobased Terephthalic Acid Technologies: A Literature Review, Ind. Biotech., 10, 91, 10.1089/ind.2014.0002

Schenk, N.J., Biesbroek, A., Heeres, A., and Heeres, H.J. (2015). Process for the Preparation of Aromatic Compounds. (Patent WO 2,015,047,085 A1).

(2017, October 01). DuPont Tate & Lyle BioProducts Report. Available online: http://www.cosmoschemicals.com/uploads/products/pdf/technical/susterra-propanediol-89.pdf.

(2017, August 19). Bio-Based World News Report. Available online: https://www.biobasedworldnews.com/novamont-opens-worlds-first-plant-for-the-production-of-bio-based-butanediol-on-industrial-scale.

Kawasaki, 2005, Synthesis, thermal and mechanical properties and biodegradation of branched polyamide 4, Polymer, 46, 9987, 10.1016/j.polymer.2005.06.092

Winnacker, 2016, Biobased Polyamides: Recent Advances in Basic and Applied Research, Macromol. Rapid Commun., 37, 1391, 10.1002/marc.201600181

Moran, 2016, Biorenewable blends of polyamide-4,10 and polyamide-6,10, J. Appl. Polym. Sci., 133, 43626, 10.1002/app.43626

Schouwer, 2015, Pd-catalyzed decarboxylation of glutamic acid and pyroglutamic acid to bio-based 2-pyrrolidone, Green Chem., 17, 2263, 10.1039/C4GC02194K

Winnacker, 2015, New insights into synthesis and oligomerization of ε-lactams derived from the terpenoid ketone (−)-menthone, RSC. Adv., 5, 77699, 10.1039/C5RA15656D

Winnacker, 2014, Synthesis of Novel Sustainable Oligoamides Via Ring-Opening Polymerization of Lactams Based on (−)-Menthone, Macromol. Chem. Phys., 215, 1654, 10.1002/macp.201400324

Gandini, 2008, Polymers from Renewable Resources: A Challenge for the Future of Macromolecular Materials, Macromolecules, 41, 9491, 10.1021/ma801735u

Gandini, 2009, The furan counterpart of poly (ethylene terephthalate): An alternative material based on renewable resources, J. Polym. Sci. Part A Polym. Chem., 47, 295, 10.1002/pola.23130

Sousa, 2015, Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: A tribute to furan excellency, Polym. Chem., 6, 5961, 10.1039/C5PY00686D

Knoop, 2013, High molecular weight poly(ethylene-2,5-furanoate); critical aspects in synthesis and mechanical property determination, J. Polym. Sci. Part A Polym. Chem., 51, 4191, 10.1002/pola.26833

(2017, August 19). Avantium YXY Technology Website. Available online: https://www.avantium.com/yxy/yxy-technology/.

(2017, August 07). Avantium Report. Available online: https://www.coebbe.nl/sites/default/files/documenten/nieuwsbericht/491/PEF%20Polyester%20-%20Ed%20de%20Jong.pdf.

Gomes, 2011, Synthesis and characterization of poly(2,5-furan dicarboxylate)s based on a variety of diols, J. Polym. Sci. Part A Polym. Chem., 49, 3759, 10.1002/pola.24812

Tsanaktsis, 2014, Thermal degradation kinetics and decomposition mechanism of polyesters based on 2,5-furandicarboxylic acid and low molecular weight aliphatic diols, J. Anal. Appl. Pyrolysis, 112, 369, 10.1016/j.jaap.2014.12.016

Jiang, 2012, A series of furan-aromatic polyesters synthesized via direct esterification method based on renewable resources, J. Polym. Sci. Part A Polym. Chem., 50, 1026, 10.1002/pola.25859

Papageorgiou, 2016, Production of bio-based 2,5-furan dicarboxylate polyesters: Recent progress and critical aspects in their synthesis and thermal properties, Eur. Polym. J., 83, 202, 10.1016/j.eurpolymj.2016.08.004

Avantium Report (2017, August 07). Furanics: Versatile Molecules Applicable for Biopolymers Applications. Available online: http://www.soci.org/-/media/Files/Conference-Downloads/2009/Bioplastic-Processing-Apr-09/Jong.ashx?la=en.

Storbeck, 1993, Synthesis and properties of polyesters based on 2,5-furandicarboxylic acid and 1,4:3,6-dianhydrohexitols, Polymer, 34, 5003, 10.1016/0032-3861(93)90037-B

Jiang, 2015, A biocatalytic approach towards sustainable furanic–aliphatic polyesters, Polym. Chem., 6, 5198, 10.1039/C5PY00629E

Jiang, 2016, Enzymatic synthesis of 2,5-furandicarboxylic acidbased semi-aromatic polyamides: Enzymatic polymerization kinetics, effect of diamine chain length and thermal properties, RSC Adv., 6, 67941, 10.1039/C6RA14585J

Jiang, 2014, Enzymatic Synthesis of Biobased Polyesters Using 2,5-Bis(hydroxymethyl)furan as the Building Block, Biomacromolecules, 15, 2482, 10.1021/bm500340w

Pfister, 2015, Synthesis and Ring-Opening Polymerization of Cyclic Butylene 2,5-Furandicarboxylate, Macromol. Chem. Phys., 216, 2141, 10.1002/macp.201500297

Ilarduya, 2016, Poly(alkylene 2,5-furandicarboxylate)s (PEF and PBF) by ring opening polymerization, Polymer, 87, 148, 10.1016/j.polymer.2016.02.003

Liu, 2007, Synthesis of Polymandelide: A Degradable Polylactide Derivative with Polystyrene-like Properties, Macromolecules, 40, 6040, 10.1021/ma061839n

Cairns, 2017, A broad scope of aliphatic polyesters prepared by elimination of small molecules from sustainable 1,3-dioxolan-4-ones, Polym. Chem., 8, 2990, 10.1039/C7PY00254H

Buchard, 2014, Preparation of Stereoregular Isotactic Poly(mandelic acid) through Organocatalytic Ring-Opening Polymerization of a Cyclic O-Carboxyanhydride, Angew. Chem. Int. Ed., 53, 13858, 10.1002/anie.201407525

Jing, 2008, Bifunctional Monomer Derived from Lactide for Toughening Polylactide, J. Am. Chem. Soc., 130, 13826, 10.1021/ja804357u

Yin, 1999, Preparation and Characterization of Substituted Polylactides, Macromolecules, 32, 7711, 10.1021/ma9907183

Satoh, 2006, Biomass-derived heat-resistant alicyclic hydrocarbon polymers: Poly(terpenes) and their hydrogenated derivatives, Green Chem., 8, 878, 10.1039/b607789g

Satoh, 2014, Sustainable cycloolefin polymer from pine tree oil for optoelectronics material: Living cationic polymerization of β-pinene and catalytic hydrogenation of high-molecular-weight hydrogenated poly(β-pinene), Polym. Chem., 5, 3222, 10.1039/C3PY01320K

Li, 2014, Cationic copolymerization of 1,3-pentadiene with α-pinene, J. Polym. Eng., 34, 583, 10.1515/polyeng-2014-0062

Miyaji, 2016, Bio-Based Polyketones by Selective Ring-Opening Radical Polymerization of a-Pinene-Derived Pinocarvone, Angew. Chem. Int. Ed., 55, 1372, 10.1002/anie.201509379

Singh, 2012, Synthesis and Characterization of Polylimonene: Polymer of an Optically Active Terpene, J. Appl. Polym. Sci., 125, 1456, 10.1002/app.36250

Sharma, 2006, Radical co-polymerization of limonene with N-vinyl pyrrolidone: Synthesis and characterization, Des. Monomer Polym., 9, 503, 10.1163/156855506778538001

Kleij, 2016, Terpolymers Derived from Limonene Oxide and Carbon Dioxide: Access to Cross-Linked Polycarbonates with Improved Thermal Properties, Macromolecules, 49, 6285, 10.1021/acs.macromol.6b01449

Byrne, 2004, Alternating Copolymerization of Limonene Oxide and Carbon Dioxide, J. Am. Chem. Soc., 126, 11404, 10.1021/ja0472580

Auriemma, 2015, Stereocomplexed Poly(Limonene Carbonate): A Unique Example of the Cocrystallization of Amorphous Enantiomeric Polymers, Angew. Chem. Int. Ed., 54, 1215, 10.1002/anie.201410211

Auriemma, 2015, Crystallization of Alternating Limonene Oxide/Carbon Dioxide Copolymers: Determination of the Crystal Structure of Stereocomplex Poly(limonene carbonate), Macromolecules, 48, 2534, 10.1021/acs.macromol.5b00157

Kobayashi, 2009, Controlled Polymerization of a Cyclic Diene Prepared from the Ring-Closing Metathesis of a Naturally Occurring Monoterpene, J. Am. Chem. Soc., 131, 7960, 10.1021/ja9027567

Sarkar, 2016, Green Approach toward Sustainable Polymer: Synthesis and Characterization of Poly(myrcene-co-dibutyl itaconate), ACS Sustain. Chem. Eng., 4, 2129, 10.1021/acssuschemeng.5b01591

Kaneko, 2004, Thermotropic Liquid-Crystalline Polymer Derived from Natural Cinnamoyl Biomonomers, Macromol. Rapid. Commun., 25, 673, 10.1002/marc.200300143

Kaneko, 2006, Environmentally degradable, high-performance thermoplastics from phenolic phytomonomers, Nat. Mater., 5, 966, 10.1038/nmat1778

Tateyama, 2016, Ultrastrong, Transparent Polytruxillamides Derived from Microbial Photodimers, Macromolecules, 49, 3336, 10.1021/acs.macromol.6b00220

Puanglek, 2016, In vitro synthesis of linear α-1,3-glucan and chemical modification to ester derivatives exhibiting outstanding thermal properties, Sci. Rep., 6, 1, 10.1038/srep30479

Kanetaka, 2016, Preparation of Poly(ether ketone)s Derived from 2,5-Furandicarboxylic Acid via Nucleophilic Aromatic Substitution Polymerization, J. Polym. Sci. Part A Polym. Chem., 54, 3094, 10.1002/pola.28193